Demi Moore's Worst Looks Ever

The town of Roswell, New Mexico — one of the most mysterious places in America — is home to more than just ufology attractions. It's also the birthplace of Demi Moore, an A-list megastar who has been a popular figure in Hollywood for nearly four decades. As Interview Magazine notes, one of her early big breaks was as "investigative reporter Jackie Templeton on the classic soap opera General Hospital" in the 1980s. The star went on to become a member of the legendary "Brat Pack," and then starred alongside Patrick Swayze in the Academy Award-winning film Ghost. Her career has continued to spin on, not unlike a ghost-operated potter's wheel.

Outside of acting, Moore has also gotten a lot of attention for her love life. First, she was hitched to rock musician Freddy Moore. Then, there was her relationship with Bruce Willis. And after that, there was her marriage to Ashton Kutcher, which was a major hit with the tabloids. All of the years spent in the spotlight and under the media's watchful eye have given Moore a chance to showcase her sense of style. She has had a lot of huge fashion wins over the years, but every now and again, her ensembles are nothing but trouble. And even as Moore continued to prove in 2020 that she is one of the hottest women alive, she probably wishes she could take back some fashion choices from the past. 

Look away ... or look closer at Demi Moore's worst looks ever.

For all the scientists out there, St. Elmo's Fire is a "weather phenomenon involving a gap in electrical charge," kind of like lightning, according to How Stuff Works. It's also the name of the 1985 "coming-of-age film starring a young Emilio Estevez" and Demi Moore. It was the second movie in 1985, after The Breakfast Club, to feature what became known as the "Brat Pack." The crew of young actors from the two films also hung out together outside of filming. Which brings us to the outfit she wore the day she took this photo with Estevez.

Moore's hairstyle is very '80s in the worst kind of way with gigantic bangs and hair that is simultaneously in a bun and also flowing down her back. The herringbone wool coat is stylish but way too big. It would be better at keeping the entire Brat Pack warm at the same time.

In this busy year for the former soap actor, Moore divorced from her first husband whom she married at 18 years old. But she also met Estevez on the set of St. Elmo's Fire and the two even planned a wedding together for 1986. The couple broke off the engagement and took wildly different paths forward. Moore moved on to even bigger fame while Estevez ultimately moved away from the spotlight.

After Brat Pack members Demi Moore and Emilio Estevez called off their engagement, the two remained friends. And in fact, Estevez played the role of cupid for Moore's next love interest at the premiere of his 1987 film Stakeout. Estevez reportedly introduced his ex-fiancé to another man, Bruce Willis. Just one year later, Willis would become the next big action hero in one of the best action and Christmas movies ever, Die Hard. Moore "talks about her first impression of Willis, describing him as 'cocky, dark, and handsome,'" in her memoir Inside Out, via Entertainment Tonight. The actor didn't hide his infatuation with Moore, "prompting Estevez to tell her, 'He's all over you, like a cheap suit in the rain.'" Willis reportedly "asked her on a date before the night was over" and the two were married that same year, 1987, "just four months after meeting." And the two welcomed their first child, Rumer Willis, in 1988.

The celebrity couple appeared seemingly everywhere together, including here in 1989 at the 61st Oscars. For the occasion, Moore wore a fashion cape with a decorative golden lining that matched the golden lining on her bustier. On top, she wore a long-sleeved, lace shirt with an extremely scooped neckline to show off that gilded bustier. Plus, the top morphs into what looks like a pair of bike shorts, except with a decorative bottom hemline. Maybe Moore should leave capes to the superheroes?

In 1991, Demi Moore and Bruce Willis welcomed their second child, Scout Willis. And fully into their status as a power couple in Hollywood, Moore and Willis rolled into the '90s hopping around to different events. Here, in 1992, the two were at a screening of the film A Few Good Men in New York City. The legal drama stars Tom Cruise and Jack Nicholson's iconic improvised line. And it showcased a screenplay by writer Aaron Sorkin, based on his Broadway play of the same name. Surrounded by the biggest names in Hollywood, Willis sported the casual looking but iconic Ralph Lauren Polo Bear sweater, which debuted one year earlier, according to GQ. Moore, however, went a completely different route.

She wore a black three-piece pinstripe suit with a peak-lapel. Moore paired the suit with a crisp white, spread-collar shirt, thick purple tie with a tie pin, polka-dotted pocket square, and gray suede gloves. And to top it all off, a black bowler hat. Though perfectly suited for a Halloween party, this get-up made no sense. The movie was about Marines in court, but Moore looked like a roaring '20s banker. Did she forget what year it was?

In the early 1990s, Demi Moore became increasingly famous based on the success of films like Ghost and continued to land roles alongside the biggest names in Hollywood. Here in 1993, she is with her husband Bruce Willis at the premiere of Indecent Proposal in Beverly Hills. Moore starred in the film as the object of desire alongside Robert Redford and Woody Harrelson, yet her choice of outfit for the premiere is anything but seductive. First, Moore is hardly ever seen with glasses, and this particular silhouette of eyewear is a bit of a miss. The round wire frames don't exude the coolness of John Lennon, but rather a dorky, Harry Potter-esque style. Her middle part with two pin-straight pigtails only adds to the geek-chic vibe. For the outfit, an ultra-wide, peak-lapel suit jacket, retro collar shirt collar buttoned wide open to reveal a clashing beaded necklace seems completely random. Or rather, indecent.

Despite the big name actors, the movie received mostly negative press. For example, Los Angeles Times commented on the tired stereotype of the "love-for-sale plot gimmick, portraying women as voluptuous poker chips or contested territory in male sexual rivalries." The film missed on a basic plot level too, with a storyline "so ridiculous, you wouldn't believe me if I told you," The Washington Post reviewed.

In 1991, a British entrepreneur named Robert Earl opened "a Hollywood-themed restaurant chain backed by major Hollywood stars," via Economic Times. Who are those stars, you ask? Why, they were Bruce Willis, Sylvester Stallone, Demi Moore, and Arnold Schwarzenegger, and yes, they all attended the restaurant openings. When the Planet Hollywood opened for business in Disney World in 1994, Moore showed up wearing a black velvet jacket, as you can see in this photo she took with actor Melanie Griffith... who also happens to be in velvet. Long live the '90s, and long live that extremely long blazer. Now, if you only saw Moore's black patent shoes and that luxe coat, you might think it was a more formal event. But then, the light-washed jeans show up and really bring the casual. On Planet Hollywood, dissonance is fashion. 

And finally, her pose with Griffith is equal parts charming and awkward prom photo. Moore had reasons to smile beyond a trip to the restaurant's Disney World location. She and Willis welcomed their third child together that same year in 1994. The couple's daughter and the youngest of the Willis sisters, Tallulah Willis, would go on to become the non-actor of the family.

Years after the first Planet Hollywood opening, Bruce Willis and Demi Moore still made cameos at new locations of the restaurants, like here in 1995. Bruce Willis looks like a polished businessman. Moore on the other hand, looks like she just rolled out of bed. First, there's the curly hair that she couldn't bother to brush away from her face. But mainly, it's the dress that also appears to be a nightgown. The white silk fabric is pretty but the dress is very short and very wrinkled, which makes her look like a poorly dressed ghost at Halloween. Plus, the look is a little odd paired with shiny, heeled sandals.

Despite the casual appearance, Moore was poised for a big milestone in the entertainment industry. For her 1996 film Striptease, The Guardian reports she received $12.5 million for the part, making her the highest-paid actress at the time. "The day that happened to me, when I got that deal, I was really grateful. It changed the business for all women," she told The Independent. "The sum itself is inconsequential. The mark in time that women are finding an equivalent box office response to men is what's more important. The attitude changing is more important." And though, as Screen Rant points out, Striptease cleaned up at the Razzies, Moore's payday fortunately started a positive shift in remuneration for actresses in Hollywood.

Sporting a shocking buzz cut, Demi Moore starred in one of her most iconic roles in the 1997 film G.I. Jane. But after the movie, she briefly retired from acting to become a stay-at-home mom in Idaho. One year later, in 1998, she separated from husband Bruce Willis and the two divorced in 2000.

Then in the early aughts, following some big life changes, Moore resurfaced in Hollywood. In this 2003 photo, Moore is at the premiere of The Matrix Reloaded, the highly anticipated action sequel. In a movie series known for black and leather outfits, Moore questionably decided to wear light-washed jeans. And pink. Shiny, shimmery blush pink. Her skin-tight, no-shoulder top features tiger-patterned stripes of rose gold glitter. Moore paired the top with ripped jeans that also appear to be stained? Plus, they are so long that she's stepping on the bottoms of the pants with her sandals. Unlike The Matrix trilogy, this outfit does not deserve a second look.

After Demi Moore's widely publicized split from Bruce Willis, she still appeared to be thriving. The Ghost star played a supporting role as a villain in Charlie's Angels: Full Throttle alongside Cameron Diaz, Lucy Liu, Drew Barrymore, and Justin Theroux doing his best Irish accent. "Moore, 40, looks great in a bikini and doesn't even try to act," Rolling Stone recapped. "Moore is 40 and looks fabulous, and Moore is a mother with a friendly ex-husband," the Los Angeles Times reiterated at the Hollywood premiere of the film in 2003. Moore showed up with Willis, their children, and "if appearances are to be believed, a 25-year-old lover." This "young photogenic boyfriend" was Ashton Kutcher.

This photo from that same year shows Moore and Kutcher attending an afterparty in New York following a screening of Charlie's Angels: Full Throttle. She has an amazing forest green, velvet jacket with a light mint green satin bow ... that totally went to waste draped over her arm. And her ruffled, jade chiffon dress is practically falling off. Plus fishnets. Plus velvet green shoes. Plus a shiny green purse. There's a lot of green and a lot of textures, to say the least. 

The bold ensemble is a Yves Saint Laurent ready-to-wear look from when Tom Ford was at the helm, and it probably worked better on the runway. 

At age 42, Demi Moore married the much younger Ashton Kutcher, then 27, in 2005. People reported the two tied the knot about two years after they "met at a casual dinner in New York City." This was Moore's third attempt at marriage. But even with three children from her relationship with Bruce Willis, her new husband Kutcher assimilated well into the family. Kutcher said he and the three young women would "talk about everything," and that the Willis sisters referred to him as MOD: "My Other Dad."

The late September wedding means this photo from October 2005 shows the couple only a few weeks into marriage.  However, it seems Moore was a little too relaxed on her outfit matching abilities here in New York City during the honeymoon phase. Each component is fine by itself; the luxurious brown leather bag is nice, and the fit of the cropped jeans and sweater is great. However, the color combination is all over the place. An orange top, paired with blue jeans, gray flats, a green hat, and a sand-colored jacket do not work together. And for accessories, the way-too-big glasses (hello, 2005!) are second worst to the floppy, emerald knit cap.

At the 2010 European premiere of Valentine's Day in London, Demi Moore showed up to support her husband, Ashton Kutcher. The film featured a star-studded cast including Julia Roberts, Bradley Cooper, Jamie Foxx, Kutcher, and Taylor Swift giving a shot at acting. Even with all the star power, the movie turned out to be rather forgettable with only a charming gag-reel. But Moore's outfit here in London is unforgettably bad.

The dress is a structured strapless sheath that is exaggerated at the hip points. The silhouette almost works, but there's some strange puckering and draping at the top. Furthermore, it looks like she folded a napkin around her chest to prevent any spills. Or like someone taped used tissues to a little black dress. Or like paper cranes in an origami-gone-wrong moment. And for a movie called Valentine's Day, where is the red?

In 2012, Demi Moore and Ashton Kutcher filed for divorce. The high-profile couple's six-year-long marriage ended in the wake of cheating rumors, and their separation got a lot of attention from the press. During the fallout, Kutcher remembered his "name splashed across every gossip magazine as an adulterer," he told Vanity Fair.

After her messy split from Kutcher, Moore continued to make appearances around Los Angeles. And she continued to make some bold style choices, with mixed results. Like this photo from 2014 where Moore attended The De Rey Gallery art opening in Los Angeles. The top and bottom of the satin pant suit look to be ever-so-slightly different shades of white. And the pant component is wrinkled. The shade of orange of her peep toe wedges totally mismatches Moore's tan leather jacket. Plus, the shoes awkwardly display two very uncomfortable looking toes. 

Demi Moore's fascinating life story seems similar to the Hollywood films that helped shape her career. To share her crazy-but-true experiences, Moore penned Inside Out, which quickly joined the list of other shocking celebrity memoirs. And inside of Inside Out, the star talks about her marriages to Bruce Willis and Ashton Kutcher. Speaking about her relationship with the much younger Kutcher, Moore said, "[I was enjoying] a do-over, like, I could just go back in time and experience what it was like to be young, with him — much more so than I'd ever been able to experience it when I was actually in my twenties," Us Magazine quoted from the book.

Here in 2019, at a New York City Barnes & Noble, Moore celebrated the release of her book. And while the pages featured shocking stories, Moore's outfit at the event was shocking for the wrong reasons. It appears like a weird take on a workwear uniform, or maybe a pajama set with a belt on top. The whole look seems... off. Are the pants supposed to be that long? Why is there a belt? And did you catch the square toe boots?

As a staple in Hollywood, Demi Moore's activities around town earn her seemingly as much press as her films and her dating history. (Remember the rumor that she dated Nick Jonas after her daughter Rumer Willis connected the pair? You better believe that report got buzz in 2018!) In this photograph from 2019, Moore is at a launch event for a book titled Fashion in LA. Hey, after a career of wearing exquisite dresses and outfits from the biggest designers in the world — "the epitome of understated glamour," according to Harper's Bazaar — it seems fitting that she attends events that celebrate fashion.

The outfit she chose, however, raises some questions. Moore's black dress with stripes in a desert color palette on the sleeves and bottom fits feels very plain. And the dress fits just a bit too loosely, and the thigh-high, black suede boots make the whole thing look more like an apron. At least the silk scarf matches the trim on the dress? An all-around underwhelming showing, especially given that it was for a book called Fashion in LA.